A Different Upper East Side
by BlairWaldorfxo
Summary: Spotted: Two hunks & a blonde, apparently "detectives" wanting to know about the killings happening at Constance and St Judes. What's going on? I'll be the first to know. You Know You Love Me xoxo Gossip Girl. SPN/GG X-Over. Blair/Dean Sam/Ruby.


_**Fanfiction - Supernatural/Gossip Girl**_

_Disclaimer; I don't own anything in this fic apart from my own storylines and characters. Supernatural and Gossip Girl each belong to the CW._

**Authors Note; So this is my first cross-over fic, I've decided to write it because Gossip Girl + Supernatural are my two favourite on air shows, so it only makes sense to do a cross over fic! This is gonna be a Sam+Ruby fic, even though there will be hints of Ruby+Dean, as you'll see. It's also gonna be Blair+Dean, just because I think they'd work well together. In this fic, the deal thing never happened, so Dean's not gonna die, and he was never going to die because of the deal. I'm not sure what's happening with the Nate, Chuck and Blair situation, I'll just see how that goes, although Chuck+Nate will be friends in this fic. So, please read, review and enjoy! xo**

**CHAPTER ONE;**

Maria Rynes stepped down from the steps of Constance Billard School for girls, she left the gates and waited for her limo to pick her up. It was 8PM, and the day was rapidly fading away. She had just spent the entire afternoon and beginning of the evening finishing her History assignment, and had a storming headache so was eager to return home. As she waited on the curb of the road, her cell phone began to vibrate. **1 New Msg from Gossip Girl xo.** She clicked the ignore tab, for once she didn't have time or a care in the world to read Gossip Girl's latest dish, she just wasn't in the mood this evening. A brisk wind swept past her, with a salty taste in the air arriving with it. She quickly turned her head. The deserted street seemed to have a sudden eerie presence. "Hello?" Maria called. No answer. She shivered, and checked her cell phone for the time. _"Youuu,"_ something whispered. "Who is that?" Maria demanded. For no more than a second after Maria spoke these words, she let out a scream. "HEEELPPP," she called, but it was late, she was dead a minute later.

* * *

"Argh," Dean moaned, shutting the door of his beloved 1967 Chevvy Impala, in an angered way.

"Dean, we haven't even been here a day and you're already moaning," his brother Sam said.

"That's because I can't even see this becoming a good job for us. Wow, a couple of high school kids have died in the last month, that's why you're Mommy and Daddy tell you to not do drugs," Dean sarcastically, said.

"Dean, how many times? None of the pupils that have died from drugs, alchohol, wounds, anything. It's like something just killed them inside. I don't know, that's why we're here, it's gotta be something supernatural," Sam explained.

"Yeah, but why here? I hate this town".

"First, off it's a city, and it's New York, you love New York!"

"Yeah, not this part, though, it's so.."

"Rich?"

"My thoughts exactly. Now we do wanna actually get to work today, ya hear that Blondie? Get outta the car!" Dean ordered to Ruby. Things were always like this between Dean and Ruby. She'd been hunting with them for about a month now, and even though she was a demon, she became a great help at times. Dean had found it especially hard to adjust to the fact that Ruby was here to stay, hunting had always been his and Sam's thing. Brothers.

"If you want to actually get anywhere with this job, then I wouldn't talk to me like that again, got it?" Ruby argued back. Her hair was in loose curls today, and she was wearing black jeans and a white top with a black bow in the middle.

"Why want you gonna do? Pull your demon crap on me?" He teased.

"You wanna bet, I won't?"

"Okay, okay. Guys, stop. Look we've gotta pull this story off, in order for them to let us in the school in the first place. So, chill. And take my lead."

"Okay, Mr Bigshot, whatever you say. By the way, I'll be vacuuming the car later, you know in case Ruby stained it," Dean said as they crossed the road towards the two schools.

"Actually, I did, you see I was drinking a carton of orange juice, and somehow it just sorta spilt all over the backseat. Sorry, I guess I shoulda wiped it straight away, we wouldn't want your precious car to get sticky now, would we?" Ruby winked.

"You just wait, I'll get you, you know that?" Dean threatened, but in a way that wasn't so deameaning.

"Bring it on bigshot, bring it on".

They soon found themselves outside the office that joined Constance Billard School for Girls, and the St Jude's school for boys together.

"We all know what we're doing right?" Sam made sure. He often found himself the leader of their hunting jobs, and had to make sure everyone knew their roles, when they were working with 'ordinary' people.

"Yes, Fred", Dean commented, even Ruby had to laugh at this joke, even if it was pretty lame.

"Okay. Here we go then, I 'spose," Sam walked in first with Dean behind him and Ruby last. The two schools joined in the middle, they shared assemblies together and also had one reception. A brunette woman was on the front desk, she wore black rimmed glasses and had her hair in a half up half down style, Sam guessed she was around 30. "May I help you?" The woman whose name tag read 'Elisabeth Jakobs', spoke as she put the phone down onto the reciever.

"Hi," Sam announced. "I'm Sam Young, and this is my brother Dean," he said gesturing Dean. "Hi," Dean smiled back, "And this is my girlfriend, Ruby.."

Ruby stepped forward, "Ruby... Ribbon," she smiled. Dean glared at her, "Ruby Ribbon?" He muttered under his breath, Ruby kicked him in a not so gentle way.

"Oh, you're hear for the assembly?" Elisabeth asked, filing through various sheets of papers.

"That's right," Sam told her.

"Okay, I just need for you to sign, here, here and herel," She showed them. "After you're done, just make your way down the corridor and Headmistress Queller will see you from there," she smiled.

"Thank you," Dean nodded.

They each took a turn to sign the paper with their fake names and afterwards walked down the corridor in a line of three with Sam in the middle.

"Ruby Ribbon? What the hell are you playing at?" Dean hissed, "Do you want us to get caught out? I'm sure even _you _could think of a more believable name than that!"

"What's wrong with Ruby Ribbon? It's better than Sam and Dean Young, that's probably the most common name on the planet!" Ruby argued back.

Sam flung his hands out either side of him, to motion the other two to hault. "Will you STOP? God, anyone would have thought you were an old married couple. We need to make this believable. We need to know what the _hell _is happening at these two schools, and we're not gonna be able to do that if you two don't shut up! So are ya ready?" Sam asked getting increasingly aggravated by the second.

"Sorry, Sammy," Ruby whispered and squeezed his cheek.

"Hey," Dean pointed, "Only I can call him Sammy,".

The three of them carried on esculating down the corridor until they saw a woman who was probably in her mid to late fifties waiting for them.

"Hello there, I'm Headmistress Queller of Constance Billard School for Girls, you must be the counsellors we're expecting?" She asked offering her hand for each of them to shake, she then gestured for them to sit in the three empty chairs in the hallway.

"That's right," Sam answered her, "You have a lovely school here, Headmistress", he complemented her. _Keep 'em sweet, good boy Sammy_, Dean thought.

"Why thank you," she blushed, "Now the assembly doesn't begin for another fifteen minutes, so in that time I'm eager to here about this business of yours," she raised her eyebrow along with a smile that showed her teeth.

"Well," Dean began, "It's just a small family run business, we have a small office in Brooklyn, our father started it up back in the day," Dean laughed.

"I see. So do many teenagers come to you for advice?" She asked, interested.

Lying through his teeth once more, Dean began, "Many, yes. Sam and I here, we're professionals, we love to help kids, make sure they get the best possible life they deserve,". Headmistress Queller's face lit up, whilst Ruby just stared at him, _damn these boys were good liars, their father had trained them good afterall._

"And you're also detectives?" She questioned them

"That's right," Dean told her.

"So, where do you come in, Miss..?" Headmistress Queller stopped realising she didn't have a clue who the blonde girl was sitting between the two brothers.

"Miss Ribbon," she smiled, "Ruby Ribbon. I'm Sam here's girlfriend," she said, wrapping her arm around Sam's shoulder, "We've been together for about two years now. Two, blissful wonderful years," she said giving him a kiss on the cheek.

"Aww, isn't that lovely?" the headmistress quality, "What about you, dear? Have you got a girlfriend? Or is that too personal?" She quickly realised what she was asking of him.

Dean laughed, "Not at the moment, no," he answered straight out.

"Okay. Well, I should go into the hall, make sure the pupils are ready for you. Why don't you sort out whatever you have to, and I'll send my secretary to get you in around seven minutes?"

"Sounds good," Ruby commented.

Headmistress Queller walked off, her heels making a noise the whole way down the corridor. When she was out of sight, Dean spoke, "How are we gonna last a whole assembly?" He whispered.

Sam got his laptop out of the briefcase he had with him and switched it on. "The powerpoint presentation I have prepared will last around twenty minutes and after that we'll ask them if they have any questions for us, give them our contact details, go back to the motel for lunch, and then this afternoon we're gonna be conducting one on one interviews with the senior class, seeing as they knew the kids that died. It's pretty simple, really," Sam spoke them through the plan.

The three of them sat in an awkward silence, the only sound was coming from Dean's feet, where he was tapping his shoe against the floor.

"Would you mind, you know, not doing that?" Ruby asked him. He stopped. Around three minutes later he started again, but before Ruby could tell him off again, a Blonde woman appeared in front of them, she was wearing a trouser suit and had her hair clipped back.

"The students are just gathering into the hall, Headmistres Queller would like you to join them now," she smiled, leading the way. "Just sit, over there," she whispered pointing at three empty seats.

"Good morning students," the Headmistress began. "I know it must be incredibly hard for you to be here with us, after the shock deaths of some of your fellow peers, but this morning's assembly is incredibly important. I'd like to introduce you to Dean, Sam and Ruby. They're professional counsellors and also run a small detective agency, who regularly work with young people such as yourselves, helping them with issues such as sex, drugs & alcohol,".

"My three favourite things," Chuck Bass whispered to his best friend Nate Archibald. They were sitting on the left hand side of the hall, along with the other St Jude's boys, and as usual Chuck was bored out of his brains.

"So if you'd like to take it from here?" She asked, gesturing the three hunters to step forward.

"Okay, um Good Morning. I'm Sam, this is my girlfriend Ruby,"

"Hi," she smiled.

"Now that is hot," Chuck commented.

"Chuck, the guy just said she's his girlfriend," Nate whispered.

"Yeah, and? You think that'll stop me?" Chuck asked.

"Well I guess it hasn't before," Nate laughed, shaking his head.

"And this is my brother, Dean," Dean waved. "So, we've basically come here today because, we've been quite concerned at the number of deaths that have happened at these two schools recently. So today, 3rd period onwards each senior student will have a sort of interview with the three of us to discuss these awful happenings and how they've effected you. First of all though we've planned a presentation," Sam announced and flicked through the slides.

After 20 minutes the assembly ended, and the students began to file out.

"So back to the motel?" Dean asked.

"I guess," Sam agreed.

"Good, I'm STARVING," He announced and began to walk out of the hall, when he noticed a brunette girl standing, almost waiting for them.

"Shouldn't you be at class?" Dean asked her.

"Yes," she admitted, "But I think there's something you should know, first."

"What?" Ruby asked, now eager to find out what the girl had to say.

"I think I know what's happening with the killings," Blair Waldorf told them.


End file.
